Water → p-Toluenesulfonic acid

Participants

Reaction Conditions

Reaction Steps

Phenoxanol (30.00 g, 0.168 mol) and pyridine (130 mL) are combined in a flask fitted with a condenser, internal thermometer, mechanical stirrer and argon inlet. The solution is cooled to -10° C. and to it is added p-toluenesulfonyl chloride (39.28 g, 0.202 mol) in portions via Gooch tubing so as to maintain the reaction temperature between -10°-0° C. After 3 h, water (20 mL) is added in portions so as to keep the temperature of the reaction below 5° C. The reaction mixture is warmed to room temperature and then poured into a separatory funnel containing 275 mL of ether. The layers are separated and the organic layer is washed with 5M H2SO4 (75 mL), saturated CuSO4 solution (75 mL), water (2×75 mL) and saturated NaHCO3 solution (75 mL). After drying over MgSO4, the organic layer is filtered and concentrated to leave a light yellow liquid as phenoxanyl p-toluenesulfonate. Purity of the product is determined by thin layer chromatography and the structure confirmed by 1H and 13C NMR.

Provenance & Evidence